4-Cyano-2-fluorobenzoic acid → HCID 178511968, compound

HRID 1020922Notes

Reaction equation

[C:1]([C:3]1[CH:36]=[CH:35][C:6]([C:7]([NH:9][C@H:10]([C:18]2[NH:19][CH:20]=[C:21]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[N:33]=C(C)O[N:30]=4)=[CH:25][CH:24]=3)[N:22]=2)[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:8])=[C:5]([F:37])[CH:4]=1)#[N:2].C(C1C=CC(C(O)=[O:45])=C(F)C=1)#N>>[C:29]([C:26]1[CH:25]=[CH:24][C:23]([C:21]2[N:22]=[C:18]([C@@H:10]([NH:9][C:7](=[O:8])[C:6]3[CH:35]=[CH:36][C:3]([C:1]([NH2:2])=[O:45])=[CH:4][C:5]=3[F:37])[CH2:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:19][CH:20]=2)=[CH:28][CH:27]=1)(=[NH:30])[NH2:33]

Participants

Reactant 2

HCID 5906594-Cyano-2-fluorobenzoic acid

HCID 178432475HCID 178432475, compound

Product 1

HCID 178511968HCID 178511968, compoundYield 90%

Procedure

Part C: 4-Cyano-2-fluoro-N—((S)-1-{4-[4-(5-methyl-[1, 2,4]oxadiazol-3-yl)-phenyl]-1H-imidazol-2-yl}-2-phenyl-ethyl)-benzamide: The compound of Example 183 Part B was coupled to 4-cyano-2-fluorobenzoic acid using the procedure of Example 176 Part B to provide the amide in 90% yield. 1H NMR (500 MHz, CDCl3) δ ppm 2.64 (s, 3H) 3.43 (dd, J=13.75, 7.15 Hz, 1H) 3.58 (dd, J=13.75, 7.70 Hz, 1H) 5.38 (q, J=7.15 Hz, 1H) 7.20-7.33 (m, 7H) 7.42 (d, J=9.90 Hz, 1H) 7.54 (d, J=8.25 Hz, 2H) 7.86 (s, 1H) 8.05 (d, J=8.25 Hz, 2H) 8.14 (t, J=7.70 Hz, 1H) 9.43 (s, 1H). m/z 493.1 (M+H)+.

Sources & evidence

ORD record: ord-0acd448b92ad4c32a74aef1d14c2b691
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08716492B2

Reaction notes

Loading…